It's always darkest before the dawn
by uesgirl
Summary: Chuck is the dark knight who's desperately looking to finally find the light in his life. Life is full of twists and turns, and sometimes the end might seem just like the beggining. Jenny's world is about to change when something tells her that she might be the one to find Chuck's lost soul. Once you're in with the Bass there's no way to get out.
1. Prologue

A.N. I will ship Chenny until the world ends. _I can pretend that I'm not lonely, but I'll be constantly fooling myself. I can pretend that it don't matter, but I'll be sitting here lying to myself..._

Disclaimer: I do not own Gossip Girl, if I did I would have never screwed up Jenny in season 3. She was so much more than that.

**Sometimes I wonder how I would look at him now, if Dan and Serena had ****never made it in time last year...**

Honestly, It's hard for me to open up to people. My problem is that I always tend to only see the best in them. I've got burnt so many times because of my own wrong assumptions that I'm starting to lock myself out. It's always easier to be harsh and self-centered, than to be vulnerable. That's where our opinions coincide.

I opened up to Chuck that night at the "Kiss on the lips" party... He forced himself on me.

But what's weird is that I never thought that he would've gone any further than just pressing his rough lips against my skin. He was desperately wanting for me to give in. Every since then I haven't stopped thinking about the pain in his eyes that always seemes to haunt him whenever he is around me. It almost feels like he's waiting for someone to make him believe that he can be more than this; more than the Chuck Bass that everyone knows.

They say that eyes are the mirror of the soul. That's not always right. It's impossible to see the reflection of Chuck's soul, his soul is behind of an oppressive wall and the only way to it is straight through that wall.

After his apology for what he did to me last year I couldn't stop thinking about him. About the disgust that I saw in his eyes when he was telling me how sorry he was. He gave a promise to me; a promise that when I'll move in with Lily and my dad, he won't be around...

I couldn't do it, I just couldn't... Lily was the only family that he had and once Chuck would be completely alone he would slowly destroy himself. The only thing that could save him (if that's even possible) was pure love. People who would love him for no matter what, people who wouldn't wait for anything in exchange, someone to be his; without regrets, secrets, hurt and schemes.

I couldn't let Chuck go. He needs everything that was left from whatever used to be his family. He needs Lily, Eric, Serena and now Dan and Rufus too.

And like it or not he needs me too. I was determined to get to his soul; and once I had made my mind there was no way back.

A few taps on my shoulder severed my thoughts and I turned my head to see my father's thoughtful face.

"Jenny we're here," he smiled and rolled out of the cab to step on the street outside the Van der Woodsen's penthouse, "It's time for a new beggining."

He was right. It really is.

**I know that this chapter is pretty short but it's just a prologue. I would really appreciate your reviews, suggestions and critical remarks. Pretty much just anything that's on your mind. :)**


	2. In The Next Room

**A.N.** So this is the first full chapter to this story. I hope that you liked the way I've portrayed the characters. I will try my best not to write any of them OOC.

**Disclaimer:** I do not own Gossip Girl. Never have and never will. ( Isn't this sad? :D)

* * *

I've never been so excited and scared at the sime time without any obvious reason for me to be this way. Today I'm officially in. Now I can call myself an actual member of the club; the club of wealthy and powerful. I've always wanted to get in, but now suddenly I'm getting cold feet. Just a year ago I was ready to sacrifice everything I had just to be like them, and just a few months ago I almost ruined my relationship with my dad to fulfill my unrealistic dreams. And here I am, finally getting what I was longing for all along, but for some reason it didn't feel the way I was hoping for it to feel.

I've gained Blair's respect, become the queen of Constance, forgiven Chuck and now I was about to move in to live in a luxurious penthouse in the Upper East Side. Could it get any better, you would say. But honestly I was a little bit scared. Isn't this ironic? When I finally got what I wanted, I was starting to have second thoughts. I wasn't sure if that was really what I've been aiming at for the last two years.

The elevator doors opened in front of me to reveal the glamour and luxury of my new lifestyle. I took a look at my dad to make sure he was ready to do this. He gave me an encouraging smile and I smiled back as convincingly as I could. I picked up my big bag of my favorite clothes and sucked in a huge breath as I glanced at my dad one last time over my shoulder. I finally exhaled and stepped out of the elevator with my dad following me just after a second.

"Rufus, Jenny!" Lily broke the silence expressing her excitement to finally welcome us.

I smiled at her and looked around to make me feel less awkward. I glimpsed back at her when my dad finally decided to say something.

"Hi Lil," he walked to the sofa next to Lily and put down his bags on the floor. He then gave her a sweet kiss on her lips and put his hand around her waist focusing his eyes on me. "Jenny are you going to stand by the elevator for the rest of the day?" My dad teased me about my awkward behavior and let out a light laughter.

"Um, no, I guess not," I answered as I turned to Lily. "Where should I put my bag?"

"Is that all you have?" Lily was surprised to see my only bag hanging in my skinny hand.

"No, I just decided not to encumber myself with all my belongings just now." I put down my bag on the floor and ran my neat fingers through my bangs. "I thought that I should first get used to my new room and then get some help with all my other clothes. I think that Eric will be more than happy to help me out." I smiled at Lily and Rufus when I heard steps coming down the staircase behind me.

"Did I hear someone just say my name?" Eric said as he came closer to us. He gave me a welcoming smile and leaned in for a friendly hug.

"Jenny was just telling us how you could help her with the rest of her things when she'll get used to her room." Lily said.

"Yeah, I just want to decide what exactly I'll need and where should I be putting it all." I glanced at Eric giving him a helpless look. He nodded his head and giggled just a little bit at my exaggerated need for help.

"You'll be living in the spare guest bedroom opposite Chuck's room, if that's ok with you." Lily said taking a look at Rufus and then me. "I'm sure that Serena will be more than happy to give you her room when she leaves for Brown, but until then there's not anything we can do. I hope you can understand." Lily gave me a maternal look, as if she was sorry for me having to live in the guest bedroom for a little while.

I swallowed hard and smiled back at Lily. I may have forgotten Chuck for what he did to me, or at least what he was trying to do, but too much communication wasn't exactly what I had in mind. I didn't have to be friends with him just because he was living in the same hallway; I tried to calm myself down. Eric gave me a weird look when he noticed the weird wrinkles on my forehead as I was thinking about Chuck.

"Who's hungry?" Dad distracted Eric from my face when he rubbed his hands against each other and headed to the kitchen.

"Where is he by the way?" I asked in a modest tone of voice, trying to not sound suspicious.

"You mean Chuck?" Lily asked. "I have to apologize for him not being here. I mentioned to him that you'll be moving in today, but he gave me a weird look and pleaded with a business meeting." Lily smiled at me kindly.

"Oh, and Serena's just talking to Blair on her cell phone upstairs. She'll be down in a minute." Eric informed us.

I tried to stop thinking about the fact that Chuck will be living so close to me and tried to act as casually as possible.

"What did you say about being hungry?" I nudged my dad's arm and smiled as he put it over my shoulder and led me to the kitchen. Lily and Eric followed us and sat down at the white round table.

* * *

I was enjoying my lunch when Eric asked me to pass him the big bowl of apples. I was picking it up when I saw a certain blonde coming towards the kitchen.

"Oh, I didn't know that Jenny and Rufus had already arrived." Serena said looking surprised. "I'm sorry for not joining you sooner," she apologized. "I've been talking to Blair a lot lately. She just needs a comforting friend right now."

"Oh, darling what's wrong with Blair?" Lily was concerned; she looked at Serena waiting for an answer.

"Nothing, really. She's just been feeling a little bit down lately. She told Chuck that she loved him, but he didn't say it back." Serena explained taking the empty seat next to me at the table.

"What a surprise!" Eric tried to sound shocked with a sarcastic smirk on his face.

"Eric that's not funny!" Serena gave Eric an angry look and took a sip of orange juice.

Serena tried to hide her anxious behavior, but I noticed her holding her breath when her lips opened a little bit, like she was going to say something. She smoothed down her dress on her thighs and turned to Lily.

"Mom I've been wanting to ask you something,." Serena sounded confident as always but her trembling tone gave her away.

"Yes dear?" Lily removed her glasses and waited for Serena to say something more than that.

"I was thinking on going to Europe for this summer. I'm not sure if you would approve of this idea, but I just really want to take a break from everything before college." It seemed a little bit weird to me that Serena was being so anxious about this. Even I knew that Lily would let Serena do whatever she wanted after her getting into Brown.

"Do you have an exact date in your mind?" Lily asked.

"Um, actually, I'm leaving tomorrow." Serena said artlessly.

Lily seemed a little bit surprised for a second, but then she suddenly smiled at me.

"Looks like you can have Serena's room sooner than I thought." Lily cheerfully said to me.

Serena glanced at me with _sorry _written all over her face.

"Actually, it might be better for Jenny to stay in the guest room just for a little while," Serena put her hand on mine and continued. "I'm sure that you wouldn't want to live in my mess Jenny. I'll make sure that all of my stuff is out of there before you move in." She let go of my hand and picked up a croissant from the table. "Maybe, you can take my room when you come back from Hamptons?" Serena turned to Lily and Rufus. "You are going to Hamptons this summer, right?"

Lily nodded her head and gave a sweet smile to Rufus.

"Thank you Serena, I really appreciate that." I smiled at my soon-to-be stepsister and stood up. "It was really nice talking to you all, but I'd like to get used to my new room."

"Don't forget your bag Jenny." My dad said pointing at the stack next to the sofa.

I smiled lightly and went to pick up my bag.

* * *

I was lying sleepless in my bed staring at the perfectly white ceiling. It was weird to me, to suddenly be sleeping in a completely different room. Everything in my room was so beautiful, even the candles on my nightstand. I sighed and rolled out of my bed. I was wearing cotton plaid pajamas in black and white. I glanced at myself in the mirror; my platinum blond hair was tussled and my bangs pretty much looked like they've survived a tornado. I ran my fingers through my hair trying to make it look at least a little bit neat. It was very hot in here and my forehead was covered in small drops of sweat. My pajamas didn't cover much of my skin, but it was impossible to wear something a little bit more covering because of the summer heat. No one would be in the kitchen anyways; I thought to myself and walked out of my room.

I was trying not to wake anyone so I walked on my toes to the fridge and took out a pack of milk. I checked the expiry date on the bottom of it and reached for a simple see-through glass on the counter to pour myself a glass of milk.

I took a sip of the cold fluid and walked to the round table to take a seat. I sighed and looked at the window across the room. New York really didn't sleep at all. There were city lights everywhere and I could even see the top of the Empire State Building from where I was sitting.

A low, attractive voice made me jump in my seat when I put my glass of milk on the table.

"What is it Jenny? Can't sleep?" the voice asked me in a teasing tone.

"Chuck?" I wasn't sure if my guess was right, but let's be honest, who else could it be.

"What? Were you expecting someone else?" I could tell that he had a smirk on his lips just by the tone of his voice. "Am I ruining your secret late night date?"

"No, there is no date." I retorted.

"Come here." He strongly said without giving me a chance to argue.

I awkwardly stood up from my seat and picked up my glass of milk. I cringed when I suddenly remembered about my tiny pajamas and my messy hair. I tried to pull my shorts a few inches down to make my thighs a little bit less exposed, but it didn't really work. I sighed and took a step towards the big white sofa. When I came closer I could see Chuck sitting on it with a glass in his hand; likely the fluid in it to be scotch. I sat down on the other end of the sofa and put my glass down on the coffee table in front of me.

"What are you drinking?" Chuck asked indifferently taking a sip from his glass.

"What are _you _drinking?" I answered with a question.

"I asked you first." Chuck smirked at me and licked his lips. Someone who didn't know us would think that he was flirting with me just from the tone of his raspy voice, but that was just the way Chuck liked talking to girls.

"Milk, just milk…" I caught him staring at my naked legs. "I couldn't sleep so I…" I continued in an irritated tone of voice. "Chuck!" I finally yelled when he didn't take his eyes off of me.

He didn't even bother to raise his head fast. He slowly looked away and put down his glass on the table.

"Bring me some whipped cream." He looked at my confused face with a smirk on his lips.

"What the…?" I was still extremely confused.

"Just do what I said." He seemed to be enjoying this situation and reclined on the back of the sofa.

"Fine." I retorted and stood up. I walked to the fridge checking Chuck's amused facial expression over my shoulder and took out a can of whipped cream.

Chuck was waving at me when I was coming back and pointed at the free spot on the couch next to him.

I reluctantly sat down feeling his arm rubbing against mine. I twitched because of this sudden contact that our bodies had and moved a few inches away from him.

Chuck reached for a half empty bottle of vodka and opened it completely ignoring my worried look as he poured a little bit of it a shot glass.

"Give me your milk," Chuck extended his arm in my direction waiting for me to pass him my glass.

I hesitated but then gave it to him. I flinched a little bit when his hand touched mine and then looked down at my toes. Somehow this felt extremely awkward.

"Have you ever had a _White Russian_?" Chuck asked me adding the milk from my glass to vodka. He picked up and shook the shot a little bit to mix the two fluids together.

"Um, no," I said warily.

"Take this!" he handed me the shot after he'd added a little bit of whipped cream to it.

I shook my head in non-compliance, but he was being insistent.

"Just take it," he had a grin on his face as he was enjoying my awkwardness. "It's not like it's poison."

I reluctantly took the shot from him and sniffed it.

"Now drink it," Chuck laughed at suspicious behavior.

Well he was right. It's not like it's going to kill me. I didn't really like the taste of alcohol but I swallowed the white mixture because of Chuck's insistence. I frowned as the strong taste caused a burning sensation in my throat.

"That wasn't that bad, was it?" Chuck said as he was starting to make another one.

"Now take this without making a wry face. It's too pretty to have ugly wrinkles all over it," Chuck said as he touched my chin with his thumb giving me a weird smile.

I was starting to get creeped out by his obtrusive actions. I pushed him away from my face and took the second shot. It didn't seem that bad the second time around.

Chuck watched me swallow the alcohol and then focused his entire attention on his own drink. We sat in silence for a little while when I slightly opened my mouth to say something. After a moment of hesitation I decided to ask him a question.

"What happened with you and Blair?" I asked carefully not wanting to make him angry.

Chuck froze for a second and then emptied his full glass in one go.

"It's none of your business Jenny," he retorted.

"I just…" I was trying to say something when he stopped me by raising his palm in front of my face.

"I'm tired," he looked at me with an irritated look. "You should go to your room."

I stood up when I saw his hand on his left leg clenched into a fist. There was nothing more to say.

"Goodnight Chuck," I said when I turned around and walked to my room. I put my hand on the handle and turned around hoping for him to say something. He never did.

**I hope that you like this chapter just as much as I do. Reviews are a great motivation and I really care about what you think :)**


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